New polymerization catalyzed by palladium complexes: synthesis of poly(p-phenylenevinylene) derivatives

Abstract

Palladium complexes are found to catalyze the condensation polymerization of halophenyl alkyl ketones to form polyketones, which can be readily converted to poly(phenylenevinylene) and its derivatives.

References

1. L. Cassar, J. Organomet. Chem., 1975, 93, 253; N. Miyaura and A. Suzuki, Chem. Rev., 1995, 2457; A. Dieck and R. F. Heck, J. Organomet. Chem., 1975, 93, 259; R. F. Heck, Acc. Chem. Res., 1979, 12, 146; M. Shibsaki, C. O. J. Boden and A. Kojima, Tetrahedron, 1997, 53, 7371; J. K. Stille, Angew. Chem., Int. Ed. Engl., 1986, 25, 508; T. N. Mitchell, Synthesis, 1992, 803.
2. F. Babudri, S. R. Cicco, G. M. Farinola and F. Naso, Macromol. Rapid Commun., 1996, 17, 905.
3. M. Remmers, M. Schulze and G. Wegner, Macromol. Chem. Rapid Commun., 1996, 17, 239.
4. D. K. Fu, B. Xu and T. M. Swager, Tetrahedron, 1997, 53, 15487.
5. N. Miyaki, I. Tomita and T. Endo, Polym. Bull., 1997, 39, 677; N. Miyaki, I. Tomita and T. Endo, Macromolecules, 1996, 29, 6685.
6. G. E. Wneck, J. C. W. Chien, F. E. Karasz and C. P. Lillya, Polymer, 1979, 20, 1441; I. Murase, T. Ohnishi, T. Noguchi and M. Hirooka, Synth. Met., 1987, 17, 639; J. I. Jin, Y. H. Lee and H. K. Shim, Macromolecules, 1993, 26, 1805.
7. D. J. William, Angew. Chem., Int. Ed. Engl., 1984, 23, 690; D. H. Hwang, J. I. Lee, H. K. Shim, W. Y. Hwang, J. J. Kim and J. I. Jin, Macromolecules, 1994, 27, 6000.
8. J. H. Burroughes, D. D. C. Bradley, A. R. Brown, R. N. Marks, K. Mackay, R. H. Friends, P. L. Burns and A. B. Holmes, Nature, 1990, 347, 539; G. Gustafsson, Y. Gao, G. M. Treacy, F. Klavetter, N. Colaneri and A. J. Heeger, Nature, 1992, 357, 477; P. L. Burn, A. B. Holmes, A. Krat, D. D. C. Bradley, A. R. Brown, R. H. Friend and R. W. Gymer, Nature, 1992, 356, 47.
9. R. A. Wessling and R. G. Zimmerman, Chem. Abstr., 1969, 69, 87735q; R. A. Wessling, J. Polym. Sci., Polym. Symp., 1985, 72, 55.
10. A. Greiner and W. Heitz, Macromol. Chem., Rapid Commun., 1988, 9, 581; V. P. Conticello, D. L. Gin and R. H. Grubbs, J. Am. Chem. Soc., 1992, 114, 9708.
11. M. Palucki and S. L. Buchwald, J. Am. Chem. Soc., 1997, 119, 11108.